Lawesson's reagent → HCID 178490710, compound

HRID 254673Notes

Reaction equation

HRID 254673 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:26][CH3:27])=[C:6]([CH:25]=1)[C:7](/[N:9]=[C:10]1\[S:11][C:12]2[C:22]([CH3:24])([CH3:23])[O:21][CH2:20][CH2:19][C:13]=2[N:14]\1[CH2:15][CH:16]([CH3:18])[CH3:17])=O.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:37])=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:26][CH3:27])=[C:6]([CH:25]=1)[C:7](=[S:37])/[N:9]=[C:10]1\[S:11][C:12]2[C:22]([CH3:24])([CH3:23])[O:21][CH2:20][CH2:19][C:13]=2[N:14]\1[CH2:15][CH:16]([CH3:18])[CH3:17]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 178490655HCID 178490655, compound

Product 1

HCID 178490710HCID 178490710, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of Example 89G (0.25 g, 0.61 mmol) in toluene (10 mL) was added Lawesson's Reagent (0.25 g, 0.61 mmol, Aldrich) and stirred at 80° C. for 2 hr. The reaction mixture was then cooled and concentrated. The residue was purified by column chromatography using an Analogix® Intelliflash280 ™ (SiO2, 0-50% ethyl acetate in hexanes) to afford 0.18 g (70%) of the title compound. MS (ESI+) m/z 425 (M+H)+

Workup

  1. temperatureThe reaction mixture was then cooled
  2. concentrationconcentrated
  3. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-3bb5cefd15254bd38cb0ccdcabee0ce4
Source dataset
uspto-grants-2011_01
Patent number
US07875640B2

Reaction notes

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